Close this search box.

well established and here for you

independently owned and operated since 1977

Loopty Loo : Broadway’s James Jackson Jr. Returns to Provincetown

by Steve Desroches

        Strange Loop had a strange journey. And James Jackson Jr. should know. He was there from the beginning. From the first table read in 2015 Jackson knew that the musical A Strange Loop was something special. Written by Michael R. Jackson, the story follows a young man who works as an usher at The Lion King and aspires to be a musical theater writer to tell the story of what it’s like to “travel the world in a fat, Black, queer body.” As he navigates his life, family, and aspirations, six different thoughts, each portrayed by a different actor with James Jackson Jr. as Thought 2, act as self-saboteurs as well as challenging him to overcome the obstacles to full self-expression and acceptance.

Billed as the “Big, Black and Queer American Musical,” there had never been anything like it before, which initially spooked investors and caused the musical theater establishment to turn their noses up to it. But through the persistence of those who did see the merit and potential in A Strange Loop, it landed off-Broadway at Playwrights Horizons in 2019. It received rave reviews, and the following year the entire creative team received an Obie Award, off-Broadway’s version of the Tony, and the musical won the 2020 Pulitzer Prize for Drama.

Jackson was certain this was it. After working in theater for over 20 years he was finally in a show that was headed toward the big time. Or was it? Just as A Strange Loop was about to begin a run in Washington, D.C., with plans for Broadway to follow, the pandemic shuttered theaters all over the world. Losing that momentum proved fatal to many productions as well as to some theater companies and actual brick and mortar theaters, too. All the enthusiasm and support for A Strange Loop seemed to evaporate overnight, says Jackson, and the critics of the pioneering production once again grew loud saying that when theaters did reopen A Strange Loop was too big of a risk as the theatrical world needed surefire money-makers, not ground-breaking theater. But again, those who believed in it didn’t give up and A Strange Loop went on to a run in Washington, D.C. at the Woolly Mammoth Theater Company in late 2021 and then opened on Broadway at the Lyceum Theatre, once again garnering critical acclaim, going on to win the Tony Award for Best Musical.

“It’s all a little insane, really,” says Jackson. “I have a hard time putting it into words, really. I mean, did that really happen? All of it. I mean, I remember sitting in Michael’s apartment when it was just notes on a clipboard and then off-Broadway and then a Pulitzer Prize, so somebody liked it! Then boom, the pandemic, and then we’re in D.C. during the Omicron wave, and then Broadway and then we win the top award given to us by some of the same people who said it would never work on Broadway. It all feels like a dream. But the best thing about it is seeing what it means to other people. That’s been the absolute best.”

In an era where well-meaning and important movements and cultural moments can be reduced to buzz words, Jackson had grown weary of hearing the phrase “representation matters” as it had become an “empty slogan” to him. All the talk of diversity seemed to be just that, a lot of talk, without any real structural changes. But his experiences with A Strange Loop changed that as it was a meaningful and impactful work of art. One day, after a performance that was attended by students from the American Musical and Dramatic Academy, a young transgender student went up to Jackson to say that after seeing a musical that tackled a queer identity authentically and unapologetically she finally felt like she wasn’t wasting her parents’ money by pursuing a life in the theater. There was indeed a place for her.

With A Strange Loop closing this past January, Jackson is finding that his world is opening up as well. He just finished an off-Broadway run in Michael R. Jackson’s new musical White Girl in Danger. He’s accepted a teaching position at Manhattanville College. He was invited by his alma mater Westfield State University to give the commencement address this past May, and he is increasingly becoming part of the creative fabric of Provincetown, a place he’s loved for a long, long time. He returns this holiday weekend to perform his cabaret show James Jackson Jr. Sings! at the Post Office Cabaret. A native of Randolph, Massachusetts, Jackson has been visiting Cape Cod and Provincetown, in particular, for as long as he can remember. As a gay man, the town has meant a lot to him and now as an artist he’s thrilled to work here. He first arrived to perform at Tin Pan Alley and then at their sibling stage at the Post Office. He participated this past June in the 4-Star Solo Show Festival at the Provincetown Theater and then was back at the Post Office Cabaret in August. And while he’s focusing on the upcoming shows, he has plans to be a part of Provincetown for many years to come, hoping to bring colleagues with him to perform here. But back in New York he often hears friends say that Provincetown isn’t a place for queer artists of color and they talk about its lily white reputation.

“I almost get offended by it as it’s not been my experience,” says Jackson. “I’ve felt so welcomed and supported in Provincetown. When I was there in June after a show one night I went to Spiritus Pizza. As I was waiting for my slice these two young gay Black men, I mean, I think they were 25 or younger and they were married, looked at me and then noticed a poster for my show just behind me. They were visiting for the Juneteenth holiday from Baltimore. They got so excited, as they had gone to New York to see A Strange Loop and there I was waiting for a slice of pepperoni. They treated me like I was Elvis, or something! They said this made their Provincetown trip something special and that what they had heard about the town wasn’t true. If I can be a conduit for more experiences like that in Provincetown I want to be that person. I want to share what I experience in Provincetown with everyone.”

James Jackson Jr. Sings! is at the Post Office Cabaret, 303 Commercial St., on Friday, October 6 and Saturday, October 7 at 7:30 p.m. Tickets ($35/$40) are available at the box office and online at For more information call 508.487.0087.

Recent Posts

Sign up for our Newsletter

Scroll to Top

Sign up for our Newsletter

Graphic Artist

Ginger Mountain

Ginger Mountain (MS Communications Media, BA Fine Arts/Teaching Certification K-12) has been part of the graphic design team at Provincetown Magazine since 2008. Ginger has worked as a creative director, individual contractor, and freelance designer with clients representing many areas —business software, consumer products, professional services, entertainment, and network hardware to name just a few — providing creative layout and development of a wide range of print media content. Her clients ranged from small local businesses to large corporations and Fortune 500 companies, from New Hampshire to Georgia

Keep in touch

Fill in your details and I will get back to you in no time.

Phone: + 1 508-487-1000 ext 6
[email protected] 14 Center St. Provincetown MA, 02657